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I use to have a friend who was an enormous troll. Thing is, he was extremely clever. He would come up with (and I imagine he still does this) the most unthinkable, insane, annoying and effective way to do well in competitive play. The most annoying thing he's ever made me face would have to be the following Smeargle:
Smeargle @ focus sash
Trait: Own Tempo
EVs: None
Nature: Brave
-Trick Room
-Dragon Rage
-Endeavor
-Spore

You know the strategy. First use Trick Room, while receiving an attack and dropping to 1 HP in the meantime. Then use spore to incapacitate the enemy, followed by endeavor and dragon rage, which in that order kills the opposing pokemon. He wiped out half my team, so of course I couldn't mount a comeback.

Ok some more annoying pokemon.
Darkrai. With Dark Void, Bad Dreams, AND Nasty Plot, this thing is one hell of a troll. Dark Pulse's 30% flinch rate doesnt make it any worse...and not to mention that blistering 125 speed.

Ok some more annoying pokemon.
Darkrai. With Dark Void, Bad Dreams, AND Nasty Plot, this thing is one hell of a troll. Dark Pulse's 30% flinch rate doesnt make it any worse...and not to mention that blistering 125 speed.

Really? Given his poor special defense, and the fact that he's neutral to water and electric, I've never found him too tough to beat down, even without fire attacks.

Anything with Prankster tops my list, personally. Whimsicott is the obvious annoying little bugger, but Sableye and Thundurus also get special mention. Even if you're able to beat them, they can often leave a parting gift in the form of Stun Spore/Will-o-Wisp/Thunder Wave, respectively. And that's just... infuriating.

SMod, One of the writers for the PotW, and someone you'll be hearing from often if you fail to read the rules

Anything with Prankster tops my list, personally. Whimsicott is the obvious annoying little bugger, but Sableye and Thundurus also get special mention. Even if you're able to beat them, they can often leave a parting gift in the form of Stun Spore/Will-o-Wisp/Thunder Wave, respectively. And that's just... infuriating.

Makes me believe Sapper Sipper, Flash Fire, and LightningRod/Volt Absorb all have better purposes for existing now (as well as having beneficial side-effects)

Omg. When I was clearing the Battle Tower (which I did) in HG, I fought a Milotic with the moves Double Team, Aqua Ring, Confuse Ray, and Toxic, and it was holding Leftovers. I sat there battling it for 3+ hours praying for a hit, while trying to keep my Pokemon alive.

Omg. When I was clearing the Battle Tower (which I did) in HG, I fought a Milotic with the moves Double Team, Aqua Ring, Confuse Ray, and Toxic, and it was holding Leftovers. I sat there battling it for 3+ hours praying for a hit, while trying to keep my Pokemon alive.

Lucky enough, Double Team (and all evasion moves) are banned in competitive battles and serve no purpose in double battles. But yeah, those in-game sites are brutal

This is the competitive section, therefore in-game things (such as Ferroseed in caves) do not count towards this thread.

I personally have found Amoongus to be very annoying. Mostly due to the fact that I never really prepared for it with most of my teams it really screwed with me. It's ability to cripple anyone with an 100% accurate sleep causes me to be very cautious in switching in. It's also very bulky, so even if you can get in without being put to sleep it can wear you down with either Poisoning or its attacks, or it can also cripple you with Paralysis from Stun Spore.

I managed to outstall a stallish team today using Sub Disable Gengar, he forfeited when I only had 1 shadowball left lol. Plus Gengar took out his only offensive mons. So I think it's safe to say Gengar was the most annoying mon possible for him